(5R,6R,Z)-5,6-dihydroxy-5,6-dihydro-2H-thiopyran-2-one O-methyl oxime beta-gentiobioside - Compound Card

(5R,6R,Z)-5,6-dihydroxy-5,6-dihydro-2H-thiopyran-2-one O-methyl oxime beta-gentiobioside

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(5R,6R,Z)-5,6-dihydroxy-5,6-dihydro-2H-thiopyran-2-one O-methyl oxime beta-gentiobioside

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Oxime
Canonical Smiles CO/N=C\1/C=C[C@H]([C@@H](S1)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O)O
InChI InChI=1S/C18H29NO13S/c1-28-19-9-3-2-6(21)18(33-9)32-17-15(27)13(25)11(23)8(31-17)5-29-16-14(26)12(24)10(22)7(4-20)30-16/h2-3,6-8,10-18,20-27H,4-5H2,1H3/b19-9-/t6-,7-,8-,10-,11-,12+,13+,14-,15-,16-,17+,18-/m1/s1
InChIKey RVFZVZXNAVTPPL-HAAUKZJOSA-N
Formula C18H29NO13S
HBA 15
HBD 8
MW 499.49
Rotatable Bonds 7
TPSA 220.35
LogP -4.42
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.83
Exact Mass 499.14
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Ixora undulata Rubiaceae Plantae 1231253

Showing of synonyms

  • Sugimoto S, Wanas AS, et al. (2014). Structure elucidation of secondary metabolites isolated from the leaves of Ixora undulate and their inhibitory activity toward advanced glycation end-products formation. Phytochemistry,2014,108,189-195. [View] [PubMed]
Pubchem: 172921467

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OCC2CCCC(O2)OC(S3)CC=CC3=N

Level: 2

Mol. Weight: 499.49 g/mol

Structure

SMILES: N=C1C=CCC(S1)OC2CCCCO2

Level: 1

Mol. Weight: 499.49 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 499.49 g/mol

Structure

SMILES: N=C1C=CCCS1

Level: 0

Mol. Weight: 499.49 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 499.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.02
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.370
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.750
Plasma Protein Binding
54.72
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.020
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-4.030
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.500
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.650
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-99.170
Rat (Acute)
2.240
Rat (Chronic Oral)
3.470
Fathead Minnow
2.180
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
565.870
Hydration Free Energy
-4.310
Log(D) at pH=7.4
-0.890
Log(P)
-2.75
Log S
-0.93
Log(Vapor Pressure)
-19.49
Melting Point
154.29
pKa Acid
5.62
pKa Basic
3.92
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8012
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8012
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7558
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7558
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7008
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7008

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